Reaction #1096641

Reaction equation

pyridine

triethylamine

doxorubicin hydrochloride

→

title compound

Doxorubicin

Solvents

dichloromethane

Conditions

Workup

1. 1
   Otherthe reaction mixture was dried in a vacuum oven
2. 2
   Otherto remove the solvent
3. 3
   workup.DISSOLUTIONdissolved in N,N-dimethylformamide (3 ml)
4. 4
   workup.STIRRINGwith stirring at room temperature for 1 day
5. 5
   ConcentrationThe resulting solution was concentrated
6. 6
   Otherthe residue thus obtained
7. 7
   Otherwas purified by column chromatography (dichloromethane:methanol=10:1)

Procedure

The compound obtained in Example <1-1> (55 mg, 0.0168 mmol) and p-nitrophenylchloromate (94 mg, 0.047 mmol) were dissolved in 4 ml of dichloromethane, and pyridine (68 μl, 0.084 mmol) was added thereto, followed by stirring the mixture at room temperature for 2 days. After the reaction was completed, the reaction mixture was dried in a vacuum oven to remove the solvent and dissolved in N,N-dimethylformamide (3 ml), and triethylamine (14.2 μl, 0.1 mmol) and doxorubicin-hydrochloride (13.7 mg, 0.0235 mmol; Waco Pure Chemical Industries, Ltd.) were added thereto, followed the darkroom treatment of the resulting mixture with stirring at room temperature for 1 day. The resulting solution was concentrated, and the residue thus obtained was purified by column chromatography (dichloromethane:methanol=10:1), to obtain the title compound as a red sticky solid (40.5 mg).

Source